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Chemical Papers

, Volume 72, Issue 11, pp 2893–2898 | Cite as

Bromine formation in solid NaBr/KNO3 mixture and assay of this reaction via bromination of activated aromatics

  • Ida RahuEmail author
  • Ott Kekišev
  • Jaak Järv
  • Peeter Burk
Original Paper
  • 245 Downloads

Abstract

Bromine formation in the mixture of solid NaBr and KNO3 was observed and the process was studied in different acidified organic solvent–water mixtures by monitoring the bromination of acetanilide and other compounds, containing activated aromatic substituents. This assay is based on fast bromination reaction of these aromatic compounds, as differently from the assay of Br2, the brominated aromatics can be easily determined by conventional gas chromatography–mass spectrometry (GC–MS) methods. It was found that bromine was generated autocatalytically on the surface of salt crystals and the reaction was characterized by a lag period, the duration of which depended on reaction conditions, and importantly on the type of the organic solvent in the reaction mixture. As the bromine formation could be easily controlled by reaction conditions, it was suggested that the studied reaction might have practical applications as an environmentally friendly and economically feasible bromination method. It was also shown that the bromination of aromatics followed the mechanism of classical electrophilic aromatic substitution reaction.

Keywords

Feasible in situ method of bromine formation Reaction with solid salts Eco-friendly reagents Bromination of activated aromatics 

Notes

Acknowledgements

This work was supported by the institutional research funding IUT (IUT20-15) of the Estonian Research Council.

Supplementary material

11696_2018_526_MOESM1_ESM.docx (2.5 mb)
Supplementary material 1 (DOCX 2564 kb)

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Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2018

Authors and Affiliations

  • Ida Rahu
    • 1
    Email author
  • Ott Kekišev
    • 1
  • Jaak Järv
    • 1
  • Peeter Burk
    • 1
  1. 1.Institute of ChemistryUniversity of TartuTartuEstonia

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